2-Bromo-4-fluorobenzonitrile

2-Bromo-4-fluorobenzonitrile Property

Melting point:

77-78°C

Boiling point:

262.4±25.0 °C(Predicted)

Density 

1.69±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Gray to Brown

BRN 

1940597

InChI

InChI=1S/C7H3BrFN/c8-7-3-6(9)2-1-5(7)4-10/h1-3H

InChIKey

MNNDREXLRLDWEY-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(F)C=C1Br

CAS DataBase Reference

36282-26-5(CAS DataBase Reference)

Safety

Hazard Codes 

T,Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-36/37/39-36/37-26-9

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Bromo-4-fluorobenzonitrile Chemical Properties,Usage,Production

Chemical Properties

Off-white to light yellow powder

Synthesis

General procedure for the synthesis of 2-bromo-4-fluorobenzonitrile from 2-bromo-4-fluorobenzaldehyde: In a dry 2 mL reaction vial, 2-bromo-4-fluorobenzaldehyde (3a, 0.136 g, 1 mmol, 1 eq.) and pyridine (0.474 g, 6.0 mmol, 6 eq.) were added followed by the addition of acetonitrile (2 mL) to make the concentration of 3a to be 0.5 M. Next, to the reaction vial was added Ru(bpy)3(PF6)2 (0.017 g, 0.02 mmol, 0.02 eq.), 2 (0.043 g, 0.20 mmol, 0.20 eq.), (NH4)2S2O8 (0.501 g, 2.2 mmol, 2.2 eq.), and activated 3?molecular sieves (~0.2 g). The reaction vial was sealed and placed in a blue LED reactor for 24 hours of irradiation. The temperature of the mixture was maintained at ~50 °C during the reaction without fan cooling. Upon completion of irradiation, the reaction was quenched with EtOAc and the mixture was transferred to a dispensing funnel. Additional EtOAc (30 mL) and 0.5 M HCl (aq, 30 mL) were added to separate the organic and aqueous layers. The aqueous layer was extracted with EtOAc (3 × 20 mL), and the combined organic layers were washed sequentially with 0.5 M HCl (aq, 2 × 20 mL), saturated aqueous NaHCO3 (2 × 20 mL), and brine (20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude product was adsorbed on silica gel (the amount of silica gel was 1.5 times the weight of the theoretical product) and gently loaded onto a silica gel column. The target product was first rinsed with excess hexane (about 5 times the volume of the column), and then eluted with a hexane/EtOAc solvent mixture (3-4 times the volume of the column) with a volume ratio of 90:10. The eluate was concentrated by rotary evaporation to give pure 2-bromo-4-fluorobenzonitrile (3c, 0.066 g, 50% yield) as a white solid.

References

[1] Synlett, 2018, vol. 29, # 16, p. 2185 - 2190
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7959 - 7963